JP5242876B2 - 架橋結合性または重合性プレポリマー - Google Patents
架橋結合性または重合性プレポリマー Download PDFInfo
- Publication number
- JP5242876B2 JP5242876B2 JP2001569526A JP2001569526A JP5242876B2 JP 5242876 B2 JP5242876 B2 JP 5242876B2 JP 2001569526 A JP2001569526 A JP 2001569526A JP 2001569526 A JP2001569526 A JP 2001569526A JP 5242876 B2 JP5242876 B2 JP 5242876B2
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- JP
- Japan
- Prior art keywords
- alkyl
- group
- substituted
- hydrogen
- hydroxyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 77
- 239000001257 hydrogen Substances 0.000 claims description 75
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 59
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 46
- 125000000217 alkyl group Chemical group 0.000 claims description 45
- 125000002947 alkylene group Chemical group 0.000 claims description 43
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 41
- 239000000178 monomer Substances 0.000 claims description 38
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims description 35
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 29
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
- 229920001577 copolymer Polymers 0.000 claims description 25
- 125000001424 substituent group Chemical group 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 22
- 238000000465 moulding Methods 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 239000012986 chain transfer agent Substances 0.000 claims description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- 238000004132 cross linking Methods 0.000 claims description 17
- 239000003431 cross linking reagent Substances 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 17
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 14
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 125000000524 functional group Chemical group 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 239000001301 oxygen Substances 0.000 claims description 9
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 8
- 235000000346 sugar Nutrition 0.000 claims description 8
- 125000000129 anionic group Chemical group 0.000 claims description 7
- 125000002091 cationic group Chemical group 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 150000002894 organic compounds Chemical class 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 5
- 150000001450 anions Chemical group 0.000 claims description 5
- 210000004087 cornea Anatomy 0.000 claims description 5
- 125000006686 (C1-C24) alkyl group Chemical group 0.000 claims description 4
- 229910003849 O-Si Inorganic materials 0.000 claims description 4
- 229910003872 O—Si Inorganic materials 0.000 claims description 4
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000000837 carbohydrate group Chemical group 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 239000004202 carbamide Substances 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 150000003573 thiols Chemical class 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- WLLGXSLBOPFWQV-UHFFFAOYSA-N MGK 264 Chemical compound C1=CC2CC1C1C2C(=O)N(CC(CC)CCCC)C1=O WLLGXSLBOPFWQV-UHFFFAOYSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- -1 hydroxy , Phenyl Chemical group 0.000 description 97
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 40
- 239000000243 solution Substances 0.000 description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
- 239000004971 Cross linker Substances 0.000 description 32
- 239000000203 mixture Substances 0.000 description 29
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 27
- 229920002554 vinyl polymer Polymers 0.000 description 27
- 239000002904 solvent Substances 0.000 description 21
- 239000000047 product Substances 0.000 description 20
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 19
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- 229920001296 polysiloxane Polymers 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 15
- 229920000642 polymer Polymers 0.000 description 13
- 238000002360 preparation method Methods 0.000 description 13
- 150000003839 salts Chemical class 0.000 description 13
- 238000000108 ultra-filtration Methods 0.000 description 13
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- 125000005442 diisocyanate group Chemical group 0.000 description 11
- 230000002209 hydrophobic effect Effects 0.000 description 11
- 239000007864 aqueous solution Substances 0.000 description 10
- 229920000570 polyether Polymers 0.000 description 10
- 238000000746 purification Methods 0.000 description 10
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000004721 Polyphenylene oxide Substances 0.000 description 9
- 238000000605 extraction Methods 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 239000004372 Polyvinyl alcohol Substances 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 239000012528 membrane Substances 0.000 description 8
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 8
- 230000035699 permeability Effects 0.000 description 8
- 229920002451 polyvinyl alcohol Polymers 0.000 description 8
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 7
- 229920000469 amphiphilic block copolymer Polymers 0.000 description 7
- 125000000732 arylene group Chemical group 0.000 description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
- 230000036571 hydration Effects 0.000 description 7
- 238000006703 hydration reaction Methods 0.000 description 7
- 150000002431 hydrogen Chemical class 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 125000002723 alicyclic group Chemical group 0.000 description 6
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 6
- 150000001720 carbohydrates Chemical group 0.000 description 6
- 150000001735 carboxylic acids Chemical class 0.000 description 6
- 239000004205 dimethyl polysiloxane Substances 0.000 description 6
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 6
- 239000000839 emulsion Substances 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 239000010409 thin film Substances 0.000 description 6
- OGMADIBCHLQMIP-UHFFFAOYSA-N 2-aminoethanethiol;hydron;chloride Chemical compound Cl.NCCS OGMADIBCHLQMIP-UHFFFAOYSA-N 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical group C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 229920001400 block copolymer Polymers 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000007334 copolymerization reaction Methods 0.000 description 5
- 229940097265 cysteamine hydrochloride Drugs 0.000 description 5
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 5
- 229920001515 polyalkylene glycol Polymers 0.000 description 5
- 229920001223 polyethylene glycol Polymers 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 238000001223 reverse osmosis Methods 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 4
- IEJPPSMHUUQABK-UHFFFAOYSA-N 2,4-diphenyl-4h-1,3-oxazol-5-one Chemical group O=C1OC(C=2C=CC=CC=2)=NC1C1=CC=CC=C1 IEJPPSMHUUQABK-UHFFFAOYSA-N 0.000 description 4
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 239000004743 Polypropylene Substances 0.000 description 4
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 4
- 125000003282 alkyl amino group Chemical group 0.000 description 4
- 150000001244 carboxylic acid anhydrides Chemical group 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
- 125000004956 cyclohexylene group Chemical group 0.000 description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 229920001519 homopolymer Polymers 0.000 description 4
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 description 4
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 4
- 229960004592 isopropanol Drugs 0.000 description 4
- 125000005647 linker group Chemical group 0.000 description 4
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 4
- 229920001542 oligosaccharide Polymers 0.000 description 4
- 150000002482 oligosaccharides Chemical class 0.000 description 4
- 229920001155 polypropylene Polymers 0.000 description 4
- 239000012266 salt solution Substances 0.000 description 4
- 239000000523 sample Substances 0.000 description 4
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical group O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 4
- 125000006528 (C2-C6) alkyl group Chemical group 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- GJKGAPPUXSSCFI-UHFFFAOYSA-N 2-Hydroxy-4'-(2-hydroxyethoxy)-2-methylpropiophenone Chemical compound CC(C)(O)C(=O)C1=CC=C(OCCO)C=C1 GJKGAPPUXSSCFI-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 230000001588 bifunctional effect Effects 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 125000004386 diacrylate group Chemical group 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000000017 hydrogel Substances 0.000 description 3
- 230000010220 ion permeability Effects 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- CXQXSVUQTKDNFP-UHFFFAOYSA-N octamethyltrisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C CXQXSVUQTKDNFP-UHFFFAOYSA-N 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 238000004987 plasma desorption mass spectroscopy Methods 0.000 description 3
- 239000002798 polar solvent Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 230000002000 scavenging effect Effects 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 description 3
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical group CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 3
- HDTRYLNUVZCQOY-UHFFFAOYSA-N α-D-glucopyranosyl-α-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(O)C(O)C(CO)O1 HDTRYLNUVZCQOY-UHFFFAOYSA-N 0.000 description 2
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 description 2
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- PFNHSEQQEPMLNI-UHFFFAOYSA-N 2-methyl-1-pentanol Chemical compound CCCC(C)CO PFNHSEQQEPMLNI-UHFFFAOYSA-N 0.000 description 2
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 2
- UOQHWNPVNXSDDO-UHFFFAOYSA-N 3-bromoimidazo[1,2-a]pyridine-6-carbonitrile Chemical group C1=CC(C#N)=CN2C(Br)=CN=C21 UOQHWNPVNXSDDO-UHFFFAOYSA-N 0.000 description 2
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- 239000012730 sustained-release form Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 239000003491 tear gas Substances 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- RSPCKAHMRANGJZ-UHFFFAOYSA-N thiohydroxylamine Chemical class SN RSPCKAHMRANGJZ-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 230000029663 wound healing Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- FYGDTMLNYKFZSV-BYLHFPJWSA-N β-1,4-galactotrioside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@H](CO)O[C@@H](O[C@@H]2[C@@H](O[C@@H](O)[C@H](O)[C@H]2O)CO)[C@H](O)[C@H]1O FYGDTMLNYKFZSV-BYLHFPJWSA-N 0.000 description 1
Classifications
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Description
(a)1つのエチレン性不飽和の二重結合を有する親水性モノマーの少なくとも1種と、2つまたはそれ以上のエチレン性不飽和の二重結合を含む架橋剤の少なくとも1種とを、官能基を有する連鎖移動剤の存在下で、共重合させる工程;および
(b)得られるコポリマーの1つまたはそれ以上の官能基を、エチレン性不飽和の基を有する有機化合物と反応させる工程
によって得られる、架橋結合性または重合性プレポリマーに関する。
(i)非イオン置換基
好適なアルキル置換基は、−OHおよび−NRR′〔ここで、RおよびR′は、それぞれ互いに独立して、水素または(C1〜C4)アルキルであり、好ましくは水素、メチルまたはエチル、特に好ましくは水素またはメチルである〕よりなる群から選ばれる1つまたはそれ以上の置換基で置換された(C1〜C4)アルキル(特に(C1〜C2)アルキル)であり、たとえば−CH2−NH2、−CH2−N(CH3)2である。
親水性モノマーの好適な陰イオン置換基は、特に−SO3Hおよび−OPO3H2よりなる群から選ばれる1つまたはそれ以上の置換基で置換された(C1〜C4)アルキル(特に、(C1〜C2)アルキル)であり、たとえば−CH2−SO3H;−SO3Hまたはスルホメチルで置換されたフェニル、たとえばo−、m−もしくはp−スルホフェニルまたはo−、m−もしくはp−スルホメチルフェニル;−COOH;基:−COOY4〔ここで、Y4は、−COOH、−SO3H、−OSO3H、−OPO3H2でか、または基:−NH−C(O)−O−G′(G′は、ラクトビオン酸、ヒアルロン酸、シアル酸の基である)で置換された(C2〜C6)アルキル、特に−SO3Hまたは−OSO3Hで置換された(C2〜C4)アルキルである〕;基:−CONY5Y6〔ここで、Y5は、スルホで置換された(C1〜C6)アルキル、特にスルホで置換された(C2〜C4)アルキルであり、Y6は、水素である〕、たとえば基:−C(O)−NH−C(CH3)2−CH2−SO3H;または−SO3H;あるいは適切なそれらの塩である。BまたはB′の特に好適な陰イオン置換基は、−COOH、−SO3H、o−、m−もしくはp−スルホフェニル、o−、m−もしくはp−スルホメチルフェニルまたはY5が、スルホで置換された(C2〜C4)アルキルであり、Y6が、水素である基:−CONY5Y6である。
親水性モノマーの好適な陽イオン置換基は、それぞれの場合に、−NRR′R″+An-で置換された(C1〜C4)アルキル(特に(C1〜C2)アルキル);または基:−C(O)OY7〔ここで、Y7は、それぞれの場合に、−NRR′R″+An-で置換され、さらには置換されていないか、またはヒドロキシルで置換された(C2〜C6)アルキル(特に(C2〜C4)アルキル)である。R、R′およびR"は、それぞれ互いに独立して、好ましくは水素または(C1〜C4)アルキル、より好ましくはメチルまたはエチル、特に好ましくはメチルである。適切な陰イオンAn-の例は、Hal-〔ここで、Halは、ハロゲンである〕、たとえばBr-、F-、I-、または特にCl-;さらにHCO3 -、CO3 2-、H2PO3 -、HPO3 2-、PO3 3-、HSO4 -、SO2 2-、またはOCOCH3 -のような有機酸の基である。BまたはB′の特に好適な陽イオン置換基は、Y7が、−N((C1〜C2)アルキル)3 +An-で置換され、さらにヒドロキシルで置換された(C2〜C4)アルキルであり、An-が、陰イオンである、基:−C(O)OY7、たとえば−C(O)O−CH2−CH(OH)−CH2−N(CH3)3 +An-である。
R1は、好ましくはカルボニル、エステルまたはアミド官能基、より好ましくはエステル基:−C(O)−O−である。
部分Zwの適切な陰イオン置換基は、たとえば−COO-、−SO3 -、−OSO3 -、−OPO3H-または二価の−O−PO2 -もしくは−O−PO2 -−O−、好ましくは基:−COO-もしくは−SO3 -または二価の基:−O−PO2 -−、特に基:−SO3 -である。
−C(O)O−(alk′″)−N(R)2 +−(alk′)−An- または
−C(O)O−(alk″)−O−PO2 -−(O)0-1−(alk′″)−N(R)3 +
に相当する。
−C(O)O−CH2−CH(OY8)−CH2−O−PO2 -−(CH2)2−N(CH3)3 +
で示される。
で示される。
好適なポリシロキサン架橋剤は、たとえば式(2):
で示される。
で示される基である。
に相当する。
で示されるマクロマーである。
で示されるマクロモノマーである。
である。
で示される。式(2b)のセグメントの重量平均分子量は、好ましくは、180〜6,000の範囲内にある。
である。
で示されるものである。
に従う。
R14およびR15は、それぞれ互いに独立して、水素、(C1〜C4)アルキル、フェニル、カルボキシルまたはハロゲンであり、
R16は、水素、(C1〜C4)アルキルまたはハロゲンであり、
R17およびR17′は、それぞれ2〜6個の炭素原子を有するエチレン性不飽和の基であるか、あるいは
R17およびR17′は、一緒になって、二価の基:−C(R14)=C(R16)−(R14およびR16は、上記に定義されたとおりである)を形成し、
(Alk*)は、(C1〜C6)アルキレンであり、(Alk**)は、(C2〜C12)アルキレンである〕
で示される。
R13は、好ましくは、塩素のようなハロゲン;ヒドロキシル:またはヒドロキシ(C1〜C4)アルコキシ、たとえば2−ヒドロキシエチル;特に塩素である。
変項R14およびR15の一方は、好ましくは水素であり、他方は、水素、メチルまたはカルボキシルである。最も好ましくは、R14およびR15は、それぞれ水素である。
R16は、好ましくは水素またはメチルである。
R17およびR17′は、それぞれ好ましくはビニルもしくは1−メチルビニルであるか、あるいはR17およびR17′は、一緒になって基:−C(R14)=C(R16)−(R14およびR16は、それぞれ独立して、水素もしくはメチルである)を形成する。
(Alk*)は、好ましくはメチレン、エチレンまたは1,1−ジメチルメチレン、特に基:−CH2−または−C(CH3)2−である。
(Alk**)は、好ましくは(C2〜C4)アルキレン、特に1,2−エチレンである。
H2O300g、塩化ナトリウム30gおよびNa2CO316gを、適切な反応容器内のペンタン350g中のジアミノプロピル末端ポリジメチルシロキサン(信越KF−8012、Mn≒4,000)200gの溶液に加えた。この攪拌混合物に、塩化アクリロイル10mlを約60分間で滴加し、その間混合物を室温に保った。次いで、反応混合物を、室温でさらに60分間攪拌した。
で示される化合物を清澄無色の液体として得た(0.48meq/gの二重結合)。
表に示したとおりのジアミノプロピル末端ポリジメチルシロキサンをさらに用いて、例1aの手順を繰り返した。
例1bの生成物を例1aの生成物と2.92:1の重量比で混合することによって、さらに架橋剤を製造した(0.25meq/gの二重結合)。
H2O300g、塩化ナトリウム30gおよびNa2CO316gを、適切な反応容器内のペンタン350g中のジアミノプロピル末端ポリジメチルシロキサン(信越KF−8012、Mn≒4,000)200gの溶液に加えた。この攪拌混合物に、塩化オキサリル1.97g、次いで塩化アクリロイル10mlを約60分間で滴加し、その間混合物を室温に保った。次いで、反応混合物を、室温でさらに60分間攪拌し、例1aに従って単離した(0.252meq/gの二重結合)。
温度計および冷却機器を備えた適切な容器内のビス(2−アミノエチル)アミン10gに、γ−チオブチロラクトン22gを加え、その間混合物を50℃に保った。完全に加えた後、反応混合物を80℃に加熱し、過剰なγ−ブチロラクトンを、減圧下で留去した。結晶質の生成物を、2NのHCl約48mlに溶解して、5というpH値を得た。水溶液をロータリーエバポレーターで蒸発させ、次いで生成物を減圧下で、80℃で乾燥させた。エタノールから再結晶させた後、式:
磁気攪拌棒、内部温度計、集中冷却器および乾燥管を備えた三つ口丸底フラスコに、テトラヒドロフラン(THF)120g中の例1aに従って得たポリシロキサン架橋剤76gの溶液を仕込んだ。装置を排気し、窒素を充填した。これを3回繰り返した。
類似の特性を有する両親媒性ブロックコポリマーを、下表に概説したとおりの量の化合物を用いて例2aの手順を繰り返すことにより得た。
2種類のα,ω−ビスアクリルアミド−ポリジメチルシロキサン、すなわち例1bのもの120.1gと例1aのもの43.6gの混合物を、マントルヒーターおよびサーモスタット、温度計、還流冷却器、真空/N2接続および機械的攪拌器を備えた反応器に加えた。反応器を15℃に恒温化し、PDMS混合物を、5サイクルの排気により15ミリバールまでとし、N2による掃気によって脱気した。
例2aで限外濾過前に得た反応混合物の溶媒(エタノールおよびTHF)の50体積%を、ロータリーエバポレーターで除去した。次いで、水を加え、残存する溶媒を、乳濁液の総量が約1,000mlに達するまで、ロータリーエバポレーターで除去し、反応混合物の温度を約0℃に調整した。緩衝剤(NaHCO310g)を加えた後、塩化アクリロイル8mlを、約0.8ml/分の割合で反応混合物に滴加し、その間、15%の水酸化ナトリウム水溶液の添加によって、pHを9の値で一定に保った。次いで、pHを7に調整し、反応混合物を、初めにG−3フリットを用いて濾過し、次いで300kDの膜を用いた水による限外濾過によって精製した。濃縮後、架橋結合できる生成物の10〜20%水性乳濁液が得られ、これを凍結乾燥して、白色固体を得た。
類似の特性を有する、架橋結合できる両親媒性ブロックコポリマーを、例2b〜2kの両親媒性ブロックコポリマーを用いて、例3aを繰り返すことによって得た。
例2lで得た残留乳濁液を、機械的攪拌器を備えた2リットル入りビーカーに移し、NaHCO34.0gを加え、氷浴によって混合物を1℃まで冷却した。
15%NaOH水溶液によって、pHを9.5に調整し、その値に保ち、塩化アクリロイル15mlを、0.30ml/分の割合で加えた。
沈殿管に、例3a〜3kのうちの1つの生成物2.3gと0.3重量%の光開始剤Darocure(登録商標)2959を含有するエタノール1.0gを仕込んだ。成分を、均一な粘稠溶液が形成されるまで、完全に混合した。この配合物を、5,000rpmで10分間遠心分離して、気泡を除去した。
例3lに従って得たマクロモノマーのサンプルを、ジクロロメタンに溶解した。溶液を、1.2μmのフィルター越しに加圧濾過し、ロータリーエバポレーターによって溶媒を除去した。得られた蝋状の材料のうち2.3gを、光開始剤Darocure 2959を含有する2−メチル−1−ペンタノール1.0gと混合して、清澄かつ無色の配合物を得た(粘度=7.6Pa・s、固体70.5重量%、固体に対する光開始剤0.30重量%)。
23.7gのビス(2−アミノプロピル)ポリエチレングリコール2000を、例1aに概説したとおりの方法を用いて、THF中の対応するビスアクリルアミド化合物へと転化した。ビス(2−アクリルアミドプロピル)ポリエチレングリコール10.2g、DMA8.0gおよび塩酸システアミン1.0gを、例2の方法を用いるが、溶媒として水を、触媒として1,1−アゾジイソブチルアミジンを用いて、アミン官能を有するDMA/PEGブロックコポリマーを得た。コポリマーのアミノ基を、例3aの方法を用いてアクリルアミド基へと転化した。
Nelfilcon A(アクリラート改質PVA、固体含量10%、EP-A-641806、例15iと同様にして合成)の水溶液380gに、水20ml中のH5IO62.2gを加え、Na2CO3溶液を用いてpHを7に調整した。得られた溶液を、1kD膜を用いた限外濾過によって精製して、低分子量PVA架橋剤(固体含量13.7重量%)を得た。
例6に従って得た、水性PVA架橋剤溶液77.2g(架橋剤10.6g)を、脱気し、窒素で掃気した。塩酸システアミン1.5g、DMA4.78gおよび1,1−アゾジイソブチルアミジン0.1gを加えた。反応混合物を、3回脱気し、次いで50℃で約8時間重合させた。次いで、ポリマーの溶液を、pH9および0℃の温度の過剰な塩化アクリロイルと処理した。中和した後、得られた反応液を、1kD膜を用いた限外濾過によって精製して、架橋結合性プレポリマーを得た。
DMA2.3g、N,N´−(1,2−ジヒドロキシエチレン)−ビス−アクリルアミド1.0g、塩酸システアミン1.0gおよび1,1−アゾジイソブチルアミジン0.1gを混合し、3回脱気した。次いで反応混合物を、窒素下、50℃で約8時間重合させた。ポリマーの溶液を、pH9および0℃の温度で過剰な塩酸アクリロイルと処理した。中和した後、得られた反応液を、1kD膜を用いた限外濾過によって精製して、架橋結合性プレポリマーを得た。
Claims (8)
- (a)以下の式(1a)または(1b)の親水性モノマーの少なくとも1種と、以下の式(2a)の架橋剤の少なくとも1種とを、官能基を有する連鎖移動剤の存在下で共重合させる工程;および
(b)得られたコポリマーの複数の官能基を、以下の式(9a)〜(9e)の有機化合物と反応させる工程
によって得られる架橋結合性または重合性プレポリマー:
【化1】
{式(1a)および(1b)中、R2は、水素または(C1〜C4)アルキルであり、R4は、(C1〜C4)アルキル、フェニルまたは基:−C(O)OY9(ここで、Y9は、水素か、または非置換もしくはヒドロキシルで置換された(C1〜C4)アルキルである)であり、R5は、基:−C(O)Y9′または−CH2−C(O)OY9′(ここで、Y9′は、独立して、Y9の意味を有する)であり、R3は、
(i)−OH、(C1〜C4)アルコキシおよび−NRR′(ここで、RおよびR′は、それぞれ互いに独立して、水素か、または非置換もしくはヒドロキシルで置換された(C1〜C6)アルキルもしくはフェニルである)よりなる群から選ばれる、同一または異なる1つ以上の置換基で置換された(C1〜C6)アルキル;ヒドロキシル、(C1〜C4)アルコキシまたは−NRR′(ここで、RおよびR′は、上記に定義されたとおりである)で置換されたフェニル;基:−COOY〔ここで、Yは、(C1〜C4)アルキルか、またはヒドロキシル、(C1〜C4)アルコキシ、−O−Si(CH3)3、−NRR′(ここで、RおよびR′は、上記に定義されたとおりである)、基:−O−(CH2CH2O)1−24−E(ここで、Eは、水素または(C1〜C6)アルキルである)もしくは基:−NH−C(O)−O−G(ここで−O−Gは、1〜8個の糖単位を有する糖類の基または基:−O−(CH2CH2O)1−24−E)(ここで、Eは、上記に定義されたとおりである)である)で置換された(C1〜C24)アルキルであるか、あるいはYは、非置換または(C1〜C4)アルキルもしくは(C1〜C4)アルコキシで置換された(C5〜C8)シクロアルキルであるか、あるいは非置換または(C1〜C4)アルキルもしくは(C1〜C4)アルコキシで置換されたフェニルまたは(C7〜C12)アラルキルである〕;−CONY1Y2〔ここで、Y1およびY2は、それぞれ独立して、水素、(C1〜C4)アルキルか、ヒドロキシル、(C1〜C4)アルコキシ、基:−CH(OR18)2(ここで、R18は、水素、(C1〜C4)アルキルまたは(C2〜C5)アルカノイルである)または基:−O−(CH2CH2O)1−24−E(ここで、Eは、上記に定義されたとおりである)で置換された(C1〜C12)アルキルであるか、あるいはY1およびY2は、隣接する窒素原子と一緒に、追加のヘテロ原子が皆無か、または1つの追加の酸素もしくは窒素原子を有する、五もしくは六員複素環を形成する〕;基:−OY3〔ここで、Y3は、水素、(C1〜C4)アルキルか、または−NRR′(ここで、RおよびR′は、上記に定義されたとおりである)で置換された(C1〜C12)アルキルか、または基:−C(O)−(C1〜C4)アルキルである〕;または、少なくとも1つの窒素原子を有し、該窒素原子を介してR 2 が結合した炭素原子に結合した、五ないし七員複素環の基から選ばれる、非イオン置換基;あるいは
(ii)−SO3H、−OSO3H、−OPO3H2および−COOHで置換された(C1〜C6)アルキル;−SO3H、−COOH、−OHおよび−CH2−SO3Hよりなる群から選ばれる、同一または異なる1つ以上の置換基で置換されたフェニル;−COOH;基:−COOY4〔ここで、Y4は、−COOH、−SO3H、−OSO3Hもしくは−OPO3H2でか、または基:−NH−C(O)−O−G′(ここで、G′は、陰イオン性炭水化物の基である)で置換された(C1〜C24)アルキルである〕;または基:−CONY5Y6(ここで、Y5は、−COOH、−SO3H、−OSO3Hまたは−OPO3H2で置換された(C1〜C24)アルキルであり、Y6は、独立して、Y5の意味を有するか、または水素もしくは(C1〜C12)アルキルである)から選ばれる、陰イオン置換基;あるいは
(iii)基:−NRR′R″+An−(ここで、R、R′およびR″は、それぞれ互いに独立して、水素か、または非置換もしくはヒドロキシルで置換された(C1〜C6)アルキルもしくはフェニルであり、An−は、陰イオンである)で置換された(C1〜C12)アルキル;または基:−C(O)OY7(ここで、Y7は、−NRR′R″+An−(ここで、R、R′、R″およびAn−は、上記に定義されたとおりである)で置換され、場合によりヒドロキシルで置換されていてもよい(C1〜C24)アルキルである)から選ばれる陽イオン置換基;あるいは
(iv)双性イオン置換基:−R1−Zw(ここで、R1は、直接結合またはカルボニル、カルボナート、アミド、エステル、ジカルボアンヒドリド、ジカルボイミド、ウレアもしくはウレタン基であり、Zwは、それぞれ1つの陰イオン基および1つの陽イオン基を含む脂肪族部分である)である};
【化2】
〔式(2a)中、基R6、R6′、R7およびR7′の90〜100%は、(C1〜C4)アルキルであり、基R6、R6′、R7およびR7′の0〜10%は、それぞれ独立して、アミノ(C1〜C4)アルキルまたはヒドロキシ(C1〜C4)アルキルであり、d1は、10〜300の整数であり、(alk)は、直鎖または分枝鎖(C2〜C6)アルキレンまたは基:−(CH2)1−3−O−(CH2)1−3−であり、Xは、−O−または−NH−であり、Qは、以下の式(3a)、(4a′)、(4b′)または(4c′):
【化3】
で示される基である〕;
【化4】
〔式(9a)〜(9e)中、R13は、ハロゲン、ヒドロキシル、非置換またはヒドロキシルで置換された(C1〜C6)アルコキシまたはフェノキシであり、R14およびR15は、それぞれ互いに独立して、水素、(C1〜C4)アルキル、フェニル、カルボキシルまたはハロゲンであり、R16は、水素、(C1〜C4)アルキルまたはハロゲンであり、R17およびR17′は、それぞれ2〜6個の炭素原子を有するエチレン性不飽和の基であるか、またはR17およびR17′は、一緒になって、二価の基:−C(R14)=C(R16)−(ここで、R14およびR16が上記に定義されたとおりである)を形成し、(Alk*)は、(C1〜C6)アルキレンであり、(Alk**)は、(C2〜C12)アルキレンである〕。
- 工程(a)に用いられる官能基性連鎖移動剤が、ヒドロキシル、アミノ、N−(C1〜C6)アルキルアミノまたはカルボキシル基を有する有機第一級チオールである、請求項1または2記載のプレポリマー。
- 請求項1〜3のいずれか1項記載のプレポリマーにおいて、
工程(a)での成分を、0.5〜5当量の連鎖移動剤:1当量の架橋剤:5〜60当量の親水性モノマーのモル比率で用いる、請求項1〜3のいずれか1項記載のプレポリマー。
- 請求項1〜4のいずれか1項に従って得られるプレポリマーを、型内で架橋結合させることを含む、成形物を製造する方法。
- 成形物が、眼用成形物であり、プレポリマーを、可視またはUV光を用いて、眼用型内で光架橋結合させる、請求項5記載の方法。
- 請求項5または6記載の方法によって得られる成形物。
- コンタクトレンズ、眼内レンズまたは人工角膜である、請求項7記載の成形物。
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Families Citing this family (134)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2001201723A (ja) * | 2000-01-18 | 2001-07-27 | Asahi Kasei Aimii Kk | 連続装用ソフトコンタクトレンズ |
US7879267B2 (en) * | 2001-08-02 | 2011-02-01 | J&J Vision Care, Inc. | Method for coating articles by mold transfer |
EP1474719A4 (en) * | 2002-02-15 | 2005-12-14 | Zms Llc | POLYMERIZATION PROCESS AND MATERIALS FOR BIOMEDICAL APPLICATIONS |
EP1364663A1 (en) * | 2002-05-21 | 2003-11-26 | Commonwealth Scientific And Industrial Research Organisation | Ocular devices with functionalized surface with adhesive properties |
US20030223954A1 (en) * | 2002-05-31 | 2003-12-04 | Ruscio Dominic V. | Polymeric materials for use as photoablatable inlays |
US6737448B2 (en) * | 2002-06-03 | 2004-05-18 | Staar Surgical Company | High refractive index, optically clear and soft hydrophobic acrylamide copolymers |
US20050085585A1 (en) * | 2002-10-23 | 2005-04-21 | Quinn Michael H. | Polymerizable materials |
DE602004022638D1 (de) * | 2003-02-28 | 2009-10-01 | Eyesense Ag | Biomoleküle enthaltende copolymere |
GB0327067D0 (en) * | 2003-11-21 | 2003-12-24 | Dow Corning | Polymeric products useful as oil repellents |
US20060116476A1 (en) * | 2004-12-01 | 2006-06-01 | 3M Innovative Properties Company | Hybrid thermosetting composition |
US20060116492A1 (en) * | 2004-12-01 | 2006-06-01 | 3M Innovative Properties Company | Branched polymer |
CN103933614B (zh) | 2005-02-14 | 2016-03-02 | 庄臣及庄臣视力保护公司 | 舒适的眼用器件及其制造方法 |
US9804295B2 (en) | 2005-05-05 | 2017-10-31 | Novartis Ag | Ophthalmic devices for sustained delivery of active compounds |
US7538160B2 (en) * | 2005-07-01 | 2009-05-26 | Bausch & Lomb Incorporated | Trifluorovinyl aromatic containing poly(alkyl ether) prepolymers |
US7402634B2 (en) * | 2005-07-01 | 2008-07-22 | Bausch And Lamb Incorporated | Perfluorocyclobutane copolymers |
US9052529B2 (en) | 2006-02-10 | 2015-06-09 | Johnson & Johnson Vision Care, Inc. | Comfortable ophthalmic device and methods of its production |
US8044112B2 (en) | 2006-03-30 | 2011-10-25 | Novartis Ag | Method for applying a coating onto a silicone hydrogel lens |
US7674781B2 (en) * | 2006-04-28 | 2010-03-09 | Heather Sheardown | Hyaluronic acid-retaining polymers |
US7858000B2 (en) | 2006-06-08 | 2010-12-28 | Novartis Ag | Method of making silicone hydrogel contact lenses |
TWI441835B (zh) * | 2006-07-12 | 2014-06-21 | Novartis Ag | 新穎聚合物 |
EP2077912B1 (en) * | 2006-08-07 | 2019-03-27 | The President and Fellows of Harvard College | Fluorocarbon emulsion stabilizing surfactants |
US9056880B2 (en) | 2006-09-29 | 2015-06-16 | Johnson & Johnson Vision Care, Inc. | Process for producing hydrolysis-resistant silicone compounds |
US7838698B2 (en) | 2006-09-29 | 2010-11-23 | Johnson & Johnson Vision Care, Inc. | Hydrolysis-resistant silicone compounds |
RU2450802C2 (ru) * | 2006-11-06 | 2012-05-20 | Новартис Аг | Офтальмологические устройства и способы их изготовления и применения |
WO2008060249A1 (en) * | 2006-11-17 | 2008-05-22 | Agency For Science, Technology And Research | Porous polymeric material with cross-linkable wetting agent |
EP2091979A2 (en) * | 2006-12-13 | 2009-08-26 | Novartis AG | Actinically curable silicone hydrogel copolymers and uses thereof |
AR064286A1 (es) * | 2006-12-13 | 2009-03-25 | Quiceno Gomez Alexandra Lorena | Produccion de dispositivos oftalmicos basados en la polimerizacion por crecimiento escalonado fotoinducida |
JP5473605B2 (ja) | 2006-12-21 | 2014-04-16 | ノバルティス アーゲー | 生物医学的物品のコーティング方法 |
CA2678598C (en) * | 2007-02-26 | 2015-02-03 | Novartis Ag | Method for imparting hydrogel contact lenses with desired properties |
MX2009010116A (es) * | 2007-03-22 | 2009-10-12 | Novartis Ag | Prepolimeros con cadenas polimericas que contienen polisiloxano colgante. |
JP5653624B2 (ja) * | 2007-03-22 | 2015-01-14 | ノバルティス アーゲー | 親水性ポリマー鎖を有するシリコーン含有プレポリマー |
TWI551305B (zh) | 2007-08-31 | 2016-10-01 | 諾華公司 | 相對黏稠封裝溶液之用途 |
US8119753B2 (en) * | 2007-10-23 | 2012-02-21 | Bausch & Lomb Incorporated | Silicone hydrogels with amino surface groups |
US20090111942A1 (en) * | 2007-10-25 | 2009-04-30 | Bausch & Lomb Incorporated | Method for Making Surface Modified Biomedical Devices |
US8044111B2 (en) | 2007-11-30 | 2011-10-25 | Novartis Ag | Actinically-crosslinkable silicone-containing block copolymers |
EP2232304B1 (en) * | 2007-12-10 | 2012-04-04 | Novartis AG | Method for making silicone hydrogel contact lenses |
CN101910247B (zh) * | 2007-12-12 | 2014-10-22 | 3M创新有限公司 | 包含具有聚(烯化氧)重复单元的全氟聚醚聚合物的硬质涂膜 |
RU2488863C2 (ru) | 2007-12-20 | 2013-07-27 | Новартис Аг | Способ изготовления контактных линз |
US8142835B2 (en) | 2008-01-23 | 2012-03-27 | Novartis Ag | Method for coating silicone hydrogels |
WO2010011492A1 (en) | 2008-07-21 | 2010-01-28 | Novartis Ag | Silicone hydrogel contact lenses with convertible comfort agents |
CA2730506A1 (en) | 2008-07-21 | 2010-01-28 | Novartis Ag | Silicone-containing polymeric materials with hydrolyzable groups |
WO2010056686A1 (en) * | 2008-11-13 | 2010-05-20 | Novartis Ag | Polysiloxane copolymers with terminal hydrophilic polymer chains |
AR074111A1 (es) * | 2008-11-13 | 2010-12-22 | Novartis Ag | Materiales de hidrogel de silicona con agentes humectantes unidos quimicamente |
TWI506333B (zh) | 2008-12-05 | 2015-11-01 | Novartis Ag | 用以傳遞疏水性舒適劑之眼用裝置及其製造方法 |
CN103969706B (zh) * | 2008-12-18 | 2017-08-25 | 诺华股份有限公司 | 适用于制造硅酮水凝胶接触透镜的透镜形成组合物 |
EP2379512B1 (en) | 2008-12-30 | 2017-03-29 | Novartis AG | Tri-functional uv-absorbing compounds and use thereof |
EP2408828A4 (en) | 2009-03-19 | 2013-10-09 | Agency Science Tech & Res | COPOLYMER FORMATION FROM BICONTINUE MICROEMULSION COMPRISING DIFFERENT HYDROPHILIC MONOMERS |
US8383744B2 (en) * | 2009-05-22 | 2013-02-26 | Novartis Ag | Actinically-crosslinkable siloxane-containing copolymers |
US8642712B2 (en) * | 2009-05-22 | 2014-02-04 | Novartis Ag | Actinically-crosslinkable siloxane-containing copolymers |
CA2769827C (en) * | 2009-08-24 | 2016-09-13 | Novartis Ag | Ophthalmic and otorhinolaryngological device materials |
US8431624B2 (en) * | 2009-09-15 | 2013-04-30 | Novartis Ag | Prepolymers suitable for making ultra-violet absorbing contact lenses |
AU2010314994B2 (en) | 2009-11-09 | 2016-10-06 | Spotlight Technology Partners Llc | Fragmented hydrogels |
CN102695500A (zh) | 2009-11-09 | 2012-09-26 | 聚光灯技术合伙有限责任公司 | 多糖基水凝胶 |
WO2011071790A1 (en) * | 2009-12-07 | 2011-06-16 | Novartis Ag | Methods for increasing the ion permeability of contact lenses |
TWI483996B (zh) | 2009-12-08 | 2015-05-11 | Novartis Ag | 具有共價貼合塗層之聚矽氧水凝膠鏡片 |
EP2513711B1 (en) * | 2009-12-14 | 2017-07-12 | Novartis AG | Methods for making silicone hydrogel lenses from water-based lens formulations |
US9522980B2 (en) | 2010-05-06 | 2016-12-20 | Johnson & Johnson Vision Care, Inc. | Non-reactive, hydrophilic polymers having terminal siloxanes and methods for making and using the same |
AU2011283028B2 (en) | 2010-07-30 | 2013-08-29 | Alcon Inc. | Method for making UV-absorbing ophthalmic lenses |
ES2593615T3 (es) | 2010-07-30 | 2016-12-12 | Novartis Ag | Prepolímeros anfifílicos de polisiloxano y usos de los mismos |
KR102411923B1 (ko) | 2010-07-30 | 2022-06-22 | 알콘 인코포레이티드 | 수분이 풍부한 표면을 갖는 실리콘 히드로겔 렌즈 |
HUE044765T2 (hu) | 2010-10-06 | 2019-11-28 | Novartis Ag | Polimerizálható hosszabbított láncú polisziloxánok hidrofil oldalcsoportokkal |
US8835525B2 (en) | 2010-10-06 | 2014-09-16 | Novartis Ag | Chain-extended polysiloxane crosslinkers with dangling hydrophilic polymer chains |
AU2011312206B2 (en) | 2010-10-06 | 2014-04-24 | Novartis Ag | Water-processable silicone-containing prepolymers and uses thereof |
MY159093A (en) | 2010-12-06 | 2016-12-15 | Novartis Ag | Method for making silicone hydrogel contact lenses |
WO2012082704A1 (en) | 2010-12-13 | 2012-06-21 | Novartis Ag | Ophthalmic lenses modified with functional groups and methods of making thereof |
US20130203813A1 (en) | 2011-05-04 | 2013-08-08 | Johnson & Johnson Vision Care, Inc. | Medical devices having homogeneous charge density and methods for making same |
US9170349B2 (en) | 2011-05-04 | 2015-10-27 | Johnson & Johnson Vision Care, Inc. | Medical devices having homogeneous charge density and methods for making same |
CN103597378B (zh) | 2011-06-09 | 2017-02-15 | 诺瓦提斯公司 | 具有纳米纹理化表面的硅氧烷水凝胶透镜 |
HUE029018T2 (en) | 2011-10-12 | 2017-02-28 | Novartis Ag | A method for producing UV absorbing contact lenses by coating |
KR101369381B1 (ko) * | 2011-11-04 | 2014-03-06 | 에스케이이노베이션 주식회사 | 함불소 화합물을 포함하는 저굴절 코팅 조성물, 이를 이용한 반사방지 필름, 이를 포함하는 편광판 및 표시장치 |
AU2012352003B2 (en) | 2011-12-14 | 2015-10-01 | Arrow International, Inc. | Redox processes for contact lens modification |
JP2015508425A (ja) | 2011-12-14 | 2015-03-19 | センプラス・バイオサイエンシーズ・コーポレイションSemprus Biosciences Corp. | 表面改質したコンタクトレンズ |
US9000063B2 (en) | 2011-12-14 | 2015-04-07 | Semprus Biosciences Corporation | Multistep UV process to create surface modified contact lenses |
CA2859195C (en) | 2011-12-14 | 2016-09-27 | Semprus Biosciences Corp. | Imbibing process for contact lens surface modification |
US8870372B2 (en) | 2011-12-14 | 2014-10-28 | Semprus Biosciences Corporation | Silicone hydrogel contact lens modified using lanthanide or transition metal oxidants |
KR20140143194A (ko) | 2012-03-22 | 2014-12-15 | 모멘티브 퍼포먼스 머티리얼즈 인크. | 유기-개질 실리콘 폴리머 및 이를 함유하는 하이드로겔 |
IN2014MN01864A (ja) | 2012-03-22 | 2015-07-03 | Momentive Performance Mat Inc | |
US9244196B2 (en) | 2012-05-25 | 2016-01-26 | Johnson & Johnson Vision Care, Inc. | Polymers and nanogel materials and methods for making and using the same |
CA2874718A1 (en) * | 2012-05-25 | 2013-11-28 | Johnson & Johnson Vision Care, Inc. | Polymers and nanogel materials and methods for making and using the same |
US10073192B2 (en) | 2012-05-25 | 2018-09-11 | Johnson & Johnson Vision Care, Inc. | Polymers and nanogel materials and methods for making and using the same |
US9297929B2 (en) | 2012-05-25 | 2016-03-29 | Johnson & Johnson Vision Care, Inc. | Contact lenses comprising water soluble N-(2 hydroxyalkyl) (meth)acrylamide polymers or copolymers |
US9395468B2 (en) | 2012-08-27 | 2016-07-19 | Ocular Dynamics, Llc | Contact lens with a hydrophilic layer |
JP6220404B2 (ja) | 2012-12-14 | 2017-10-25 | ノバルティス アーゲー | 両親媒性シロキサン含有ビニルモノマー及びこれらの使用 |
CA2889894C (en) | 2012-12-14 | 2017-09-12 | Novartis Ag | Actinically-crosslinkable amphiphilic prepolymers |
CA2889895C (en) | 2012-12-14 | 2017-08-29 | Novartis Ag | Amphiphilic siloxane-containing (meth)acrylamides and uses thereof |
EP2931733B1 (en) | 2012-12-14 | 2016-10-05 | Novartis AG | Tris(trimethyl siloxy)silane vinylic monomers and uses thereof |
MY172901A (en) | 2012-12-17 | 2019-12-13 | Alcon Inc | Method for making improved uv-absorbing ophthalmic lenses |
EP2951242B1 (en) | 2013-01-31 | 2019-09-11 | Momentive Performance Materials Inc. | Water soluble silicone material |
US9486311B2 (en) | 2013-02-14 | 2016-11-08 | Shifamed Holdings, Llc | Hydrophilic AIOL with bonding |
US10195018B2 (en) | 2013-03-21 | 2019-02-05 | Shifamed Holdings, Llc | Accommodating intraocular lens |
JP6838964B2 (ja) | 2013-03-21 | 2021-03-03 | シファメド・ホールディングス・エルエルシー | 調節式眼内レンズ |
US9568645B2 (en) | 2013-09-30 | 2017-02-14 | Novartis Ag | Silicone hydrogel lenses with relatively-long thermal stability |
WO2015048035A1 (en) | 2013-09-30 | 2015-04-02 | Novartis Ag | Method for making uv-absorbing ophthalmic lenses |
HUE040618T2 (hu) | 2013-10-31 | 2019-03-28 | Novartis Ag | Eljárás szemészeti lencsék elõállítására |
EP3069195B8 (en) | 2013-11-15 | 2019-07-10 | Tangible Science, LLC | Contact lens with a hydrophilic layer |
MY183117A (en) | 2013-12-13 | 2021-02-15 | Alcon Inc | Method for making contact lenses |
MY180543A (en) | 2013-12-17 | 2020-12-01 | Novartis Ag | A silicone hydrogel lens with a crosslinked hydrophilic coating |
AU2015201321A1 (en) * | 2014-03-31 | 2015-10-15 | Johnson & Johnson Vision Care, Inc. | Silicone acrylamide copolymer |
EP3134461B1 (en) | 2014-04-25 | 2018-02-14 | Novartis AG | Hydrophilized carbosiloxane vinylic monomers |
EP3134420B1 (en) | 2014-04-25 | 2019-01-30 | Novartis AG | Carbosiloxane vinylic monomers |
SG10201901379TA (en) | 2014-08-26 | 2019-03-28 | Novartis Ag | Method for applying stable coating on silicone hydrogel contact lenses |
CA2959354C (en) | 2014-08-26 | 2018-08-21 | Shifamed Holdings, Llc | Accommodating intraocular lens |
ES2914102T3 (es) | 2014-09-09 | 2022-06-07 | Staar Surgical Co | Implantes oftálmicos con profundidad de campo ampliada y agudeza visual a distancia mejorada |
EP3197940B1 (en) | 2014-09-26 | 2023-02-15 | Alcon Inc. | Polymerizable polysiloxanes with hydrophilic substituents |
WO2016079195A1 (en) | 2014-11-19 | 2016-05-26 | Solvay Specialty Polymers Italy S.P.A. | Zwitterionic derivatives of (per)fluoropolyethers |
US10160141B2 (en) | 2014-11-25 | 2018-12-25 | Novartis Ag | Molds for making contact lenses |
JP6774947B2 (ja) | 2014-12-09 | 2020-10-28 | タンジブル サイエンス インコーポレイテッド | 生体適合性層を有する医療デバイスコーティング |
US9850350B2 (en) * | 2015-03-02 | 2017-12-26 | Tokyo Ohka Kogyo Co., Ltd. | Block copolymer, method of producing block copolymer, and method of producing structure containing phase-separated structure |
US11141263B2 (en) | 2015-11-18 | 2021-10-12 | Shifamed Holdings, Llc | Multi-piece accommodating intraocular lens |
CA3004158C (en) | 2015-12-15 | 2020-06-30 | Novartis Ag | Amphiphilic branched polydiorganosiloxane macromers |
EP3391101B1 (en) | 2015-12-15 | 2020-07-08 | Alcon Inc. | Method for applying stable coating on silicone hydrogel contact lenses |
EP3419961B1 (en) | 2016-02-22 | 2020-09-02 | Alcon Inc. | Uv/visible-absorbing vinylic monomers and uses thereof |
CA3116257C (en) | 2016-02-22 | 2024-01-16 | Alcon Inc. | Uv-absorbing vinylic monomers and uses thereof |
KR102328526B1 (ko) | 2016-03-09 | 2021-11-17 | 스타 서지컬 컴퍼니 | 확장된 피사계 심도 및 향상된 원거리 시력의 안과용 임플란트 |
SG10202103737YA (en) | 2016-10-14 | 2021-05-28 | Alcon Inc | Method for producing contact lenses |
MY193482A (en) * | 2016-10-14 | 2022-10-17 | Alcon Inc | Method for producing contact lenses |
JP6783931B2 (ja) | 2016-10-26 | 2020-11-11 | アルコン インク. | 両親媒性分枝鎖状ポリジオルガノシロキサンマクロマー |
EP3554811A1 (en) | 2016-12-16 | 2019-10-23 | Novartis AG | Method for producing contact lenses |
US10350056B2 (en) | 2016-12-23 | 2019-07-16 | Shifamed Holdings, Llc | Multi-piece accommodating intraocular lenses and methods for making and using same |
US10987214B2 (en) | 2017-05-30 | 2021-04-27 | Shifamed Holdings, Llc | Surface treatments for accommodating intraocular lenses and associated methods and devices |
CN110996850B (zh) | 2017-06-07 | 2023-02-17 | 施菲姆德控股有限责任公司 | 可调节光学度数的眼内透镜 |
US10906258B2 (en) | 2017-08-29 | 2021-02-02 | Alcon Inc. | Cast-molding process for producing contact lenses |
WO2019116139A1 (en) | 2017-12-13 | 2019-06-20 | Novartis Ag | Weekly and monthly disposable water gradient contact lenses |
HUE059157T2 (hu) | 2018-01-22 | 2022-10-28 | Alcon Inc | Formaöntéses eljárás UV-t elnyelõ kontaktlencse elõállítására |
JP7292260B2 (ja) * | 2018-03-30 | 2023-06-16 | 株式会社カネカ | ポリアミド酸およびその製造方法、ポリアミド酸溶液、ポリイミド、ポリイミド膜、積層体およびその製造方法、ならびにフレキシブルデバイスおよびその製造方法 |
US10774164B2 (en) | 2018-08-17 | 2020-09-15 | Staar Surgical Company | Polymeric composition exhibiting nanogradient of refractive index |
US11459479B2 (en) | 2018-12-03 | 2022-10-04 | Alcon Inc. | Method for making coated silicone hydrogel contact lenses |
US11099300B2 (en) | 2018-12-03 | 2021-08-24 | Alcon Inc. | Method for producing coated silicone hydrogel contact lenses |
HUE061330T2 (hu) | 2018-12-14 | 2023-06-28 | Alcon Inc | Eljárás szilikon hidrogél kontaktlencsék elõállítására |
SG11202108875UA (en) | 2019-04-10 | 2021-10-28 | Alcon Inc | Method for producing coated contact lenses |
FR3095962B1 (fr) * | 2019-05-15 | 2021-10-15 | S N F Sa | Nouveau procédé de filtration de l’acide 2-acrylamido-2-méthylpropane sulfonique |
EP3976381A1 (en) | 2019-05-28 | 2022-04-06 | Alcon Inc. | Pad transfer printing instrument and method for making colored contact lenses |
WO2021038562A1 (en) * | 2019-08-26 | 2021-03-04 | Setbone Medical Ltd. | Implant comprising a plurality of hardening states |
EP4065356A1 (en) | 2019-11-26 | 2022-10-05 | Alcon Inc. | Method for producing contact lenses |
Family Cites Families (38)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4065587A (en) | 1976-05-11 | 1977-12-27 | Scm Corporation | U.V. Curable poly(ether-urethane) polyacrylates and wet-look polymers prepared therefrom |
FR2385763A1 (fr) * | 1977-03-31 | 1978-10-27 | Essilor Int | Procede de preparation de copolymeres greffes de silicones |
DE3710343A1 (de) * | 1987-03-28 | 1988-10-06 | Basf Lacke & Farben | Verzweigtes acrylatcopolymerisat mit polisierbaren doppelbindungen und verfahren zur herstellung des acrylatcopolymerisats |
US4859780A (en) * | 1988-02-26 | 1989-08-22 | Ciba-Geigy Corporation | Hydrophilic modifier monomers |
CA1318446C (en) * | 1988-05-31 | 1993-05-25 | William J. Burke | Contact lenses and materials and methods of making same |
US5158717A (en) * | 1990-11-27 | 1992-10-27 | Bausch & Lomb Incorporated | Method of molding shaped polymeric articles |
DE69121581T2 (de) * | 1990-11-27 | 1997-03-20 | Bausch & Lomb | Oberflächenaktive makromonomere |
WO1992018548A1 (en) * | 1991-04-18 | 1992-10-29 | Optical Research, Inc. | Novel composition for contact lenses |
US5310779A (en) * | 1991-11-05 | 1994-05-10 | Bausch & Lomb Incorporated | UV curable crosslinking agents useful in copolymerization |
JPH05310837A (ja) * | 1992-05-14 | 1993-11-22 | Japan Synthetic Rubber Co Ltd | 酸素透過性高分子材料の製造方法 |
US5336797A (en) * | 1992-12-30 | 1994-08-09 | Bausch & Lomb Incorporated | Siloxane macromonomers |
TW272976B (ja) | 1993-08-06 | 1996-03-21 | Ciba Geigy Ag | |
US5712356A (en) | 1993-11-26 | 1998-01-27 | Ciba Vision Corporation | Cross-linkable copolymers and hydrogels |
JPH07266443A (ja) * | 1994-03-30 | 1995-10-17 | Hoya Corp | ソフトコンタクトレンズの製造方法 |
US6342570B1 (en) | 1994-11-14 | 2002-01-29 | Novartis Ag | Cross-linkable copolymers and hydrogels |
US5665840A (en) | 1994-11-18 | 1997-09-09 | Novartis Corporation | Polymeric networks from water-soluble prepolymers |
ES2140819T3 (es) | 1995-02-03 | 2000-03-01 | Novartis Ag | Polimeros reticulados que contienen fotoiniciadores. |
ATE178414T1 (de) | 1995-02-03 | 1999-04-15 | Novartis Ag | Vernetzte polymere enthaltend ester- oder amidgruppen |
TW425410B (en) | 1995-02-03 | 2001-03-11 | Novartis Ag | Preparation of the crosslinked tinted polymers and their moldings |
TW349967B (en) | 1995-02-03 | 1999-01-11 | Novartis Ag | Process for producing contact lenses and a cross-linkable polyvinylalcohol used therefor |
TW360671B (en) | 1995-02-03 | 1999-06-11 | Novartis Ag | Process for producing mold body and the cross-linkable polymer used therein |
AU4438696A (en) | 1995-02-03 | 1996-08-21 | Novartis Ag | Crosslinked polymers |
TW448205B (en) | 1996-05-23 | 2001-08-01 | Novartis Ag | Process for the manufacture of storage-stable hydrogel-moldings |
ID17663A (id) | 1996-07-26 | 1998-01-15 | Novartis Ag | Pembuatan cetakan-cetakan |
AR008108A1 (es) | 1996-08-01 | 1999-12-09 | Novartis Ag | Un metodo para formar un articulo polimerico absorbente de radiacion, un articulo polimerico asi formado, y un metodo para formar un tintepolimerico |
AU7533696A (en) * | 1996-12-13 | 1998-06-18 | Ciba-Geigy Ag | New materials |
US5708094A (en) * | 1996-12-17 | 1998-01-13 | Bausch & Lomb Incorporated | Polybutadiene-based compositions for contact lenses |
EP0867456A1 (de) | 1997-02-04 | 1998-09-30 | Novartis AG | Ophthalmischer Formkörper |
DE69804946T2 (de) | 1997-02-21 | 2002-10-02 | Novartis Ag | Opthalmische formmasse |
JP3618951B2 (ja) * | 1997-03-14 | 2005-02-09 | 信越化学工業株式会社 | 光硬化性オルガノポリシロキサン組成物 |
US6190603B1 (en) | 1997-07-19 | 2001-02-20 | Novartis Ag | Process for producing mouldings |
US6265509B1 (en) | 1997-07-30 | 2001-07-24 | Novartis Ag | Crosslinked polymers |
US6020445A (en) * | 1997-10-09 | 2000-02-01 | Johnson & Johnson Vision Products, Inc. | Silicone hydrogel polymers |
US5981669A (en) * | 1997-12-29 | 1999-11-09 | Bausch & Lomb Incorporated | Silicone-containing prepolymers and low water materials |
JPH11287971A (ja) * | 1998-04-02 | 1999-10-19 | Kuraray Co Ltd | 眼用レンズ材料 |
US6149692A (en) | 1998-08-27 | 2000-11-21 | Novartis Ag | Method and composition for incorporating radiation-absorbing agents into polymers |
US6149842A (en) | 1998-11-12 | 2000-11-21 | Novartis Ag | Methods and compositions for manufacturing tinted ophthalmic lenses |
US5981675A (en) * | 1998-12-07 | 1999-11-09 | Bausch & Lomb Incorporated | Silicone-containing macromonomers and low water materials |
-
2001
- 2001-03-22 CA CA002401865A patent/CA2401865C/en not_active Expired - Fee Related
- 2001-03-22 BR BR0109416-5A patent/BR0109416A/pt not_active Application Discontinuation
- 2001-03-22 CN CN01806995A patent/CN1419656A/zh active Pending
- 2001-03-22 CA CA002682118A patent/CA2682118A1/en not_active Abandoned
- 2001-03-22 EP EP01933737A patent/EP1266246B1/en not_active Expired - Lifetime
- 2001-03-22 DE DE60103621T patent/DE60103621T2/de not_active Expired - Lifetime
- 2001-03-22 WO PCT/EP2001/003266 patent/WO2001071392A1/en active IP Right Grant
- 2001-03-22 ES ES01933737T patent/ES2222373T3/es not_active Expired - Lifetime
- 2001-03-22 AU AU2001260143A patent/AU2001260143A1/en not_active Abandoned
- 2001-03-22 AR ARP010101345A patent/AR029901A1/es unknown
- 2001-03-22 MX MXPA02009352A patent/MXPA02009352A/es unknown
- 2001-03-22 JP JP2001569526A patent/JP5242876B2/ja not_active Expired - Lifetime
- 2001-03-22 AT AT01933737T patent/ATE268481T1/de not_active IP Right Cessation
- 2001-03-23 US US09/815,674 patent/US7091283B2/en not_active Expired - Lifetime
-
2002
- 2002-09-18 ZA ZA200207477A patent/ZA200207477B/en unknown
- 2002-09-23 NO NO20024557A patent/NO332817B1/no not_active IP Right Cessation
-
2006
- 2006-03-21 US US11/385,418 patent/US7268189B2/en not_active Expired - Lifetime
- 2006-06-14 US US11/452,535 patent/US7238750B2/en not_active Expired - Lifetime
-
2007
- 2007-08-10 US US11/891,599 patent/US7566754B2/en not_active Expired - Lifetime
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DE60103621D1 (de) | 2004-07-08 |
MXPA02009352A (es) | 2003-02-12 |
ATE268481T1 (de) | 2004-06-15 |
NO20024557D0 (no) | 2002-09-23 |
NO20024557L (no) | 2002-09-23 |
CA2401865C (en) | 2010-01-12 |
US7238750B2 (en) | 2007-07-03 |
US20060235162A1 (en) | 2006-10-19 |
ES2222373T3 (es) | 2005-02-01 |
US7566754B2 (en) | 2009-07-28 |
JP2003528211A (ja) | 2003-09-24 |
DE60103621T2 (de) | 2005-06-16 |
NO332817B1 (no) | 2013-01-21 |
CA2401865A1 (en) | 2001-09-27 |
US20010037001A1 (en) | 2001-11-01 |
CA2682118A1 (en) | 2001-09-27 |
EP1266246B1 (en) | 2004-06-02 |
AU2001260143A1 (en) | 2001-10-03 |
EP1266246A1 (en) | 2002-12-18 |
US7091283B2 (en) | 2006-08-15 |
AR029901A1 (es) | 2003-07-23 |
US20060160957A1 (en) | 2006-07-20 |
BR0109416A (pt) | 2002-12-10 |
CN1419656A (zh) | 2003-05-21 |
ZA200207477B (en) | 2003-05-08 |
WO2001071392A1 (en) | 2001-09-27 |
US20080021127A1 (en) | 2008-01-24 |
WO2001071392A8 (en) | 2001-11-29 |
US7268189B2 (en) | 2007-09-11 |
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